Water → HCID 64318530, compound

HRID 2234405Notes

Reaction equation

HRID 2234405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[C:5]([NH:7][CH2:8][C:9]([CH3:15])([CH3:14])[CH2:10][N:11]([CH3:13])[CH3:12])=[O:6].[Cl-].[NH4+].O>C(O)C.C(O)(=O)C.[Fe]>[NH2:19][C:18]1[CH:17]=[CH:16][C:4]([C:5]([NH:7][CH2:8][C:9]([CH3:14])([CH3:15])[CH2:10][N:11]([CH3:13])[CH3:12])=[O:6])=[CH:3][C:2]=1[Cl:1]

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 686816653-chloro-N-(3-dimethylamino-2,2-dimethyl-propyl)-4-nitro-benzamide

Product 1

HCID 64318530HCID 64318530, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

3-chloro-N-(3-dimethylamino-2,2-dimethyl-propyl)-4-nitro-benzamide (2.29 g, 7.67 mmol), iron powder (2.45 g, 43.79 mmol) and ammonium chloride (781 mg, 14.60 mmol) were heated in ethanol (50 mL) and water (18 mL) at reflux for one hour. A few drops of acetic acid were added and heating continued for a further hour. The reaction mixture was cooled, filtered and the filtrate concentrated. This residue was partitioned between saturated NaHCO3 (aq.) and DCM. The organic phase was washed with brine, dried with MgSO4 and concentrated. Column chromatography gave the title compound as an orange crystalline solid. (850 mg, 39%)

Workup

  1. temperatureheating
  2. waitcontinued for a further hour
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThis residue was partitioned between saturated NaHCO3 (aq.) and DCM
  7. washThe organic phase was washed with brine
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ee4a0914a8614b13b213b599dacf18c5
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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